Explanations are a flawed method because people only go to them after they have problems, which means they'll already have decided that a) they don't understand the tool or b) the tool sucks. Once someone has decided that, it's very difficult to change their minds. That's why so many older people are terrified of computers, despite how much easier they've become. Back when they first tried, missing a comma on a command meant you had to start over. I'd be paranoid in their situation too.
What I'm still puzzled about is whether or not there's a good way to reverse that learned helplessness. The only way I've found is to throw out the existing tool and replace it with a new one. Reformatting the existing tool often doesn't work, since the underlying structure or premise is where the real problem is. The model the developer used to describe what the program does is out of sync with the model of the user. This is usually exacerbated by the fact most users can't accurately describe their models. If they could, they'd be programmers.
So now my task is to try and figure out people's models without actually asking them to describe them, since they'd probably get it wrong. I don't mean this to suggest most people are stupid, just that they don't have the skill set or experience to accurately break down something to the point a machine can understand it.
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